Synthesis of functionalized spiropyran and spirooxazine derivatives and their photochromic properties |
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| Affiliation: | 1. Hangzhou Institute of Advanced Studies, Zhejiang Normal University, 1108 Gengwen Road, Hangzhou, 311231, Zhejiang, PR China;2. Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, 310014, Zhejiang, PR China;3. Key Laboratory of Theoretical and Computational Photochemistry, Ministry of Education College of Chemistry, Beijing Normal University, Beijing, 100875, PR China;1. University of Sayyed Jamaleddin Asadabadi, Asadabad, 6541835583, Islamic Republic of Iran;2. Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Islamic Republic of Iran;3. Department of Biology, Faculty of Science, Bu-Ali Sina University, P. O. Box 65175/4161, Hamedan, Islamic Republic of Iran;1. Department of Chemistry, St. Stephen’s College, University of Delhi, Delhi 110007, India;2. Department of Chemistry, University of Delhi, Delhi 11007, India;1. School of Materials Science and Engineering, University of Science and Technology Beijing, Beijing 100083, China;2. School of Chemistry and Biological Engineering, University of Science and Technology Beijing, Beijing 100083, China |
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| Abstract: | Three series of functionalized spiropyrans and spirooxazines derivatives were synthesized and their photochromic properties were investigated in particular regard to the fatigue resistance, the lifetime of the colored merocyanine form and the interaction of the colored form molecule. (1) Spiropyrans 5 and spironaphthooxazines 6 having an antioxidant group as a pendant exhibited higher fatigue resistance than that of the parent spiro compounds in solution. In particular, spiropyrans 5 showed higher resistance than parent compound 1 in the presence of an equimolar amount of the corresponding antioxidant. (2) bis-Spironaphthooxazines 8a–8i and 10 connected through a phosphoryl group exhibited higher fatigue resistance and longer lifetime of the colored merocyanine form than those of the parent spirooxazine 7. (3) Symmetrical bis-spiro photochromic compounds 15 and 16 and unsymmetrical bis-spiro compounds 13, 14 and 17 were synthesized. The bis-spiro photochromic compounds were found to undergo intramolecular interaction between the colored merocyanine forms. |
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